Carbon tetrabromide → Methyl 4-bromo-2-(tert-butoxycarbonylamino)butanoate

Participants

Reaction Steps

A solution of triphenylphosphine (2.20 g, 8.39 mmol) in dry CH2Cl2 (20 mL) was added dropwise via syringe to a solution of N-Boc homoserine methyl ester 29 (8.39 mmol) and carbon tetrabromide (4.18 g, 12.60 mmol) in dry CH2Cl2 (20 mL). The resulting dark solution was stirred at room temperature for 16 h. Hexanes was added and precipitates were removed by suction filtration. The filtrate was concentrated under reduced pressure and subject to flash silica gel column chromatography using ethyl acetate/hexanes (1:10, v/v then 1:6, v/v) to give the desired product 30 as a yellow oil (501 mg, 20% overall yield from homoserine). 1H NMR (300 MHz, CDCl3) δ 1.45 (s, 9H), 2.12-2.48 (m, 2H), 3.39-3.47 (m, 2H), 3.78 (s, 3H), 4.33-4.48 (m, 1H), 5.10-5.22 (m, 1H). m/z (ESI) 296 [C10H18BrNO4+H]+.

Provenance & Evidence